In a perfect world, the stars would align, and would-be entrepreneurs would come up with a brilliant idea for a business while in their twenties, before a serious relationship and children, and then stumble upon a generous benefactor eager to finance their ideas. In the real world, finding the right time to strike out on your own as an entrepreneur is a real challenge. While – spoiler alert – there never is a right time to start your own business, there are some factors you’ll want to consider as you weigh your options.

 "Taking the leap into entrepreneurship is no time to be wishy-washy."

The very first determinant on whether or not it’s the right time to strike out on your own is whether or not you’ve figured out your specific purpose with your new venture, basically your “why”. Taking the leap into entrepreneurship is no time to be wishy-washy. Yes, there are elements that you can figure out along the way, but you need to be able to clearly articulate your main purpose and motivation from the start.

You’ll also want to consider whether or not you have people in your life who can support you through this career change. You’ll likely need help both personally and professionally, and so making sure you have the right relationships with the right people will be integral to your success as an entrepreneur.


You should also prepare yourself – and potentially your loved ones – for some sacrifices. These sacrifices could be financial - perhaps you, and those that depend on you, will need to really downsize your lifestyle while you build your entrepreneurial venture. Maybe the sacrifice will be less time for the people and things you love. Know that there will be sacrifices and do your due diligence to make sure that you, and others in your immediate orbit understand and are supportive of these potential sacrifices. If the people in your life aren’t onboard with your dreams, you’ll add more roadblocks onto an already uphill battle.


Youth can certainly be an asset if entrepreneurship is your goal. You have more energy, less commitments and, in most cases, less to lose. By the same token, inexperience and unpreparedness are frequently cited reasons for businesses to fail. There is often a sweet spot, where you’ve gained key business skills, but haven’t yet been weighed down with family and financial commitments. (Note that this does not mean you can’t start a business with a family – it just adds another layer of complexity).  Make sure that your experience, risk tolerance, and personal obligations all support your entrepreneurial ambitions.

 "... you don't have to have millions stashed away, nor do you have to have deep-pocketed investors lined up."

Finally, you’ll want to make sure that your finances are in order. No, you don’t have to have millions stashed away, nor do you have to have deep-pocketed investors lined up. But you do need to be sure you have money set aside to cover your living expenses for at least six months, and preferably a year. If the business requires a significant amount of capital lined up, you should have some funds available to put toward those expenses, plus you should make sure that your creditworthiness is strong if you plan to take out a business loan. You’ll want to put all your focus, energy and creativity into growing your business, so being constantly stressed about putting food on the table will certainly hamper your progress.

There truly is no right time, or right situation, to strike out on your own as an entrepreneur. Successful entrepreneurs exist in all forms – from single parents, to high schoolers, to those married with large families. Know your why, prepare, and surround yourself with supportive people and you can turn almost any situation into entrepreneurial success!

Article By

Ashleigh Finley

An ex-shopaholic, she’s now passionate about financial optimization. Her undying wish is that more people can experience financial freedom.

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